My sister Rocio and I took a spontaneous trip to Chicago last week. Chicago had been on our list of cities to see in the U.S. for a long time now so I’m so glad we got to check it off! We spent a total of 5 days in Chicago which was the perfect amount of time to see everything we wanted and more, while still finding some time to relax. I decided to create a Chicago Travel Guide with all of my favorite sights, places to eat, and places to stay! I hope you can find this guide helpful if you are planning a trip to Chicago.

What To Do

Skydeck

The Skydeck is an observatory at the top of Willis Tower. It’s an extremely popular attraction in Chicago because of the enclosed glass balcony that extends 4 feet past the side of the building, offering amazing views of the city. You can step inside the balcony for some really cool shots! The Skydeck Observatory opens at 9 am. We showed up right at opening and there was already a large crowd but it was still worth it! Buy tickets here.

Millennium Park/The Bean

Millennium Park is a large public park in Chicago where concerts and other events are held. The main attraction in Millennium Park is Cloud Gate also known as “The Bean”, a sculpture created by british Artist Sir Anish Kapoor. You can see the beautiful city skyline in the reflection of the gigantic sculpture. We got up early to avoid the crowds which was an awesome decision! We got there at about 8:30 am and there were only a few people there. We walked by later around noon and the crowds were insane!

Chicago Theatre

The beautiful Chicago Theatre holds various comedy and musical acts throughout the year. We stopped by to get some shots in front of this iconic theatre. I’m a sucker for old signs and buildings like this one!

The Magnificent Mile

The magnificent mile is the major shopping street in downtown Chicago. You’ll find dozens of high end stores, chic hotels, and cool restaurants lining this street. You can’t miss the Wrigley Building, the Chicago Tribune, and the River Bridge. At the opposite end of the magnificent mile is the historic Chicago Water Tower and the John Hancock Center. There is a bar at the top of the John Hancock Center with an amazing view of the city! Rocio isn’t 21 so she couldn’t go, but I took an elevator ride to the top just to see it. It’s a nice spot for a drink!

Riverfront

The riverfront is the perfect place to admire Chicago’s stunning architecture and skyscrapers. You can spot several boat tours passing by, including the popular architecture boat tour. We didn’t get the chance to take this tour, but I can only imagine how stunning the views are! You can book tickets here.

Lincoln Park

Lincoln Park is another public park in Chicago near the waterfront and North Beach. Lincoln Park even has a zoo and a conservatory that are both free to visit. We had a lot of fun exploring both. Since we visited in the winter, the trees and grass weren’t very green, but the park is beautiful during the spring and summer!

North Avenue Beach

North Avenue Beach is located near the end of Lincoln Park. The lake side beach is perfect for summer activities! We admired the view of Lake Michigan and the Chicago cityscape. The view is amazing! This beach is an extremely popular spot in the summer.

Wabash Arts Corridor

The Wabash Arts Corridor is full of large scale murals painted by students. We walked around for about an hour looking for different murals around every corner. My favorite was the bubblegum moose! The main area is Wabash Avenue from Van Buren to Roosevelt and from Michigan Ave to State St.

Where To Eat

Booth One

Booth One, formerly known as the legendary Pump Room, is a classic restaurant serving American Cuisine. Booth One is located on the main level of the beautiful Ambassador Hotel. This restaurant has served many celebrity guests throughout the years- booth one was the VIP table, hence the new name of the restaurant. We started off with the delicious Curried Chicken Brochette- a little spicy, crispy on the outside, and so tasty! For our main dish we had the Roast Chicken Frites. We couldn’t decide on just one dessert so we had both the Coconut Cake and the Bananas Foster Creme Pie. Both were melt-in-your-mouth good! I loved the ambience of this beautiful restaurant. Our server was amazing as well! I highly reccomend this restaurant for a fancy dining experience.

Mahalo

We loved the Hawaiian vibes at this Wicker Park neighborhood restaurant! We had the Chicken Pot Stickers, the Coconut Shrimp, and the Ahi Tuna Nachos. Our favorite dish at Mahalo was the Coconut Shrimp! I also had a delicious Big Kahuna all to myself. It was served in a pineapple! You can’t get more Hawaiian then that.

Cafe Robey

Cafe Robey is located on the main level of the beautiful art deco hotel, The Robey. We had the most amazing full course meal at the cafe. For appetizers we had the Shrimp, Pork Belly, and Trout, all of which were amazing and beautifully plated. For dinner we had the Duck and the Bass and for sides we had Gnocchi and Carrots, all of which were out of this world! If I had to choose, I would say my favorite dishes were the Bass and the side of Gnocchi. They were just too good! This beautiful cafe, located in Wicker Park is definitely worth visiting. Rocio and I have a major sweet tooth so we had to finish off with a dessert. The Dark Chocolate Mousse did not disappoint! We couldn’t have asked for better service, or a better meal.

Nellcote

This neighborhood restaurant was inspired by the French Chateau Villa Nellcote, where the Rolling Stones recorded their album “Exile on Main Street”. Rocio and I are pizza lovers, so we ordered the Sunnyside Up Organic Egg Pizza to split. We added bacon as a topping, the perfect addition to this breakfast inspired pizza! All of their flour is milled in house, so you can only imagine how great it was. Portugal the Man frequents this restaurant when they are visiting Chicago!

Goddess & the Baker

This popular bakery located downtown was bustling when we visited for a late lunch. Goddess & The Baker serves breakfast, lunch, and dinner. All of the desserts they offer look amazing, but the rainbow cake is their most popular! We shared a slice with some vanilla lattes after finishing a delicious chicken caprese panini.

Big Shoulders Coffee

We visited the Gold Coast location of this Chicago based coffee shop for our morning cup of coffee. The marshmallow lattes were insanely delicious- they even came with a roasted marshmallow on top! We also had a delicious scone with cinnamon and chocolate chips. We loved the atmosphere at Big Shoulders and the baristas were so friendly! I highly reccomend this coffee spot.

Intelligentsia Coffee

This contemporary coffee bar has several locations across Chicago. We visited the Old Town location near our hotel. I love their bold decor and color scheme! Rocio and I shared a scone and washed it down with some delicious mochas.

Where to Stay

The Blackstone Hotel

This historic hotel located right next to Millennium Park, has had many celebrity visitors through out the years from legendary mob boss Al Capone, to Nat King Cole and President Teddy Roosevelt. We stayed in a beautiful double bed room over looking the park. The room was fantastic and so was breakfast in the concourse. I love the history of this hotel! We took a tour of some of their more historic rooms. Their staff was also very friendly and helpful. I highly recommend this hotel for your stay in Chicago! Check out my Chicago Travel Guide video to see more of these spots! I would love to return to Chicago someday, maybe during the Spring or Summer. Have any of you been to Chicago?

xoxo